CA2704185C - Amino-heteroaryl-containing prokineticin 1 receptor antagonists - Google Patents

Amino-heteroaryl-containing prokineticin 1 receptor antagonists Download PDF

Info

Publication number: CA2704185C
Authority: CA; Canada
Prior art keywords: phenyl; compound; amino; formula; fluoro
Prior art date: 2007-10-30
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related

Application number

CA2704185A

Other languages

English (en)

French (fr)

Other versions

CA2704185A1 (en

Inventor

Steven J. Coats

Alexey B. Dyatkin

Wei He

Joseph Lisko

Tamara Miskowski

Janet L. Ralbovsky

Mark Schulz

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Janssen Pharmaceutica NV

Original Assignee

Janssen Pharmaceutica NV

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2007-10-30

Filing date

2008-10-23

Publication date

2016-02-16

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=40206493&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CA2704185(C) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2008-10-23 Application filed by Janssen Pharmaceutica NV filed Critical Janssen Pharmaceutica NV

2009-05-07 Publication of CA2704185A1 publication Critical patent/CA2704185A1/en

2016-02-16 Application granted granted Critical

2016-02-16 Publication of CA2704185C publication Critical patent/CA2704185C/en

Status Expired - Fee Related legal-status Critical Current

2028-10-23 Anticipated expiration legal-status Critical

Links

108010044063 Endocrine-Gland-Derived Vascular Endothelial Growth Factor Proteins 0.000 title abstract description 61
102000006402 Endocrine-Gland-Derived Vascular Endothelial Growth Factor Human genes 0.000 title abstract description 58
229940044551 receptor antagonist Drugs 0.000 title description 12
239000002464 receptor antagonist Substances 0.000 title description 12
125000005214 aminoheteroaryl group Chemical group 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 457
239000000203 mixture Substances 0.000 claims abstract description 64
-1 cyano, hydroxy, aminocarbonyl Chemical group 0.000 claims description 601
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 171
125000001424 substituent group Chemical group 0.000 claims description 140
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 100
125000001072 heteroaryl group Chemical group 0.000 claims description 74
229910052739 hydrogen Inorganic materials 0.000 claims description 72
239000001257 hydrogen Substances 0.000 claims description 72
125000000623 heterocyclic group Chemical group 0.000 claims description 59
229910052736 halogen Inorganic materials 0.000 claims description 50
150000002367 halogens Chemical class 0.000 claims description 50
125000001309 chloro group Chemical group Cl* 0.000 claims description 46
125000001153 fluoro group Chemical group F* 0.000 claims description 46
125000005605 benzo group Chemical group 0.000 claims description 44
150000002431 hydrogen Chemical class 0.000 claims description 42
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 42
125000003118 aryl group Chemical group 0.000 claims description 39
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238000000034 method Methods 0.000 abstract description 30
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125000002971 oxazolyl group Chemical group 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
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239000008177 pharmaceutical agent Substances 0.000 description 1
239000008024 pharmaceutical diluent Substances 0.000 description 1
239000002831 pharmacologic agent Substances 0.000 description 1
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FSZKLYCUEQGCKW-UHFFFAOYSA-N phenyl n-(oxomethylidene)carbamate Chemical compound O=C=NC(=O)OC1=CC=CC=C1 FSZKLYCUEQGCKW-UHFFFAOYSA-N 0.000 description 1
CWCMIVBLVUHDHK-ZSNHEYEWSA-N phleomycin D1 Chemical compound N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC[C@@H](N=1)C=1SC=C(N=1)C(=O)NCCCCNC(N)=N)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C CWCMIVBLVUHDHK-ZSNHEYEWSA-N 0.000 description 1
UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
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125000003367 polycyclic group Chemical group 0.000 description 1
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239000011148 porous material Substances 0.000 description 1
239000011591 potassium Substances 0.000 description 1
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230000003389 potentiating effect Effects 0.000 description 1
239000002243 precursor Substances 0.000 description 1
238000004237 preparative chromatography Methods 0.000 description 1
238000004321 preservation Methods 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
210000002248 primary sensory neuron Anatomy 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
230000035755 proliferation Effects 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
235000004252 protein component Nutrition 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000003072 pyrazolidinyl group Chemical group 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
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125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000001422 pyrrolinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000011946 reduction process Methods 0.000 description 1
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230000004043 responsiveness Effects 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
229910052701 rubidium Inorganic materials 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
229940081974 saccharin Drugs 0.000 description 1
235000019204 saccharin Nutrition 0.000 description 1
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
239000012488 sample solution Substances 0.000 description 1
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150000003335 secondary amines Chemical class 0.000 description 1
230000035807 sensation Effects 0.000 description 1
235000019615 sensations Nutrition 0.000 description 1
230000008313 sensitization Effects 0.000 description 1
208000026775 severe diarrhea Diseases 0.000 description 1
210000002460 smooth muscle Anatomy 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
125000003003 spiro group Chemical group 0.000 description 1
239000008107 starch Substances 0.000 description 1
238000007619 statistical method Methods 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
230000002459 sustained effect Effects 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
IKBKZGMPCYNSLU-RGVLZGJSSA-N tegaserod Chemical compound C1=C(OC)C=C2C(/C=N/NC(=N)NCCCCC)=CNC2=C1 IKBKZGMPCYNSLU-RGVLZGJSSA-N 0.000 description 1
229960002876 tegaserod Drugs 0.000 description 1
TZRQZPMQUXEZMC-UHFFFAOYSA-N tert-butyl n-(2-bromoethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCBr TZRQZPMQUXEZMC-UHFFFAOYSA-N 0.000 description 1
NVKNRJCOVHAZDK-KRWDZBQOSA-N tert-butyl n-[(2s)-6-acetamido-1-oxo-1-[[2-oxo-4-(trifluoromethyl)chromen-7-yl]amino]hexan-2-yl]carbamate Chemical compound FC(F)(F)C1=CC(=O)OC2=CC(NC(=O)[C@@H](NC(=O)OC(C)(C)C)CCCCNC(=O)C)=CC=C21 NVKNRJCOVHAZDK-KRWDZBQOSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
201000003120 testicular cancer Diseases 0.000 description 1
210000001550 testis Anatomy 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
125000004568 thiomorpholinyl group Chemical group 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
239000003053 toxin Substances 0.000 description 1
231100000765 toxin Toxicity 0.000 description 1
108700012359 toxins Proteins 0.000 description 1
230000037317 transdermal delivery Effects 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
231100000397 ulcer Toxicity 0.000 description 1
230000036269 ulceration Effects 0.000 description 1
210000002438 upper gastrointestinal tract Anatomy 0.000 description 1
JQSHBVHOMNKWFT-DTORHVGOSA-N varenicline Chemical compound C12=CC3=NC=CN=C3C=C2[C@H]2C[C@@H]1CNC2 JQSHBVHOMNKWFT-DTORHVGOSA-N 0.000 description 1
230000009278 visceral effect Effects 0.000 description 1
208000009935 visceral pain Diseases 0.000 description 1
238000010792 warming Methods 0.000 description 1
229940045860 white wax Drugs 0.000 description 1
238000002424 x-ray crystallography Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/38—Sulfur atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/06—Anti-spasmodics, e.g. drugs for colics, esophagic dyskinesia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/10—Laxatives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/12—Antidiarrhoeals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Nutrition Science (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

CA2704185A 2007-10-30 2008-10-23 Amino-heteroaryl-containing prokineticin 1 receptor antagonists Expired - Fee Related CA2704185C (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US98363807P	2007-10-30	2007-10-30
US60/983,638		2007-10-30
PCT/US2008/080915 WO2009058653A1 (en)	2007-10-30	2008-10-23	Amino-heteroaryl-containing prokineticin 1 receptor antagonists

Publications (2)

Publication Number	Publication Date
CA2704185A1 CA2704185A1 (en)	2009-05-07
CA2704185C true CA2704185C (en)	2016-02-16

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ID=40206493

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA2704185A Expired - Fee Related CA2704185C (en)	2007-10-30	2008-10-23	Amino-heteroaryl-containing prokineticin 1 receptor antagonists

Country Status (8)

Country	Link
US (2)	US8324380B2 (es)
EP (1)	EP2215067A1 (es)
JP (1)	JP2011502154A (es)
AR (1)	AR069127A1 (es)
CA (1)	CA2704185C (es)
CL (1)	CL2008003266A1 (es)
TW (1)	TWI448456B (es)
WO (1)	WO2009058653A1 (es)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
PT2399910E (pt) *	2009-02-13	2014-05-02	Shionogi & Co	Novo derivado de triazina e composição farmacéutica que contém o mesmo
JP2013533878A (ja) *	2010-06-28	2013-08-29	ヤンセンファーマシューティカエヌ．ベー．	疼痛を処置するためのプロキネチシン１受容体拮抗薬
JP2013530231A (ja) *	2010-06-28	2013-07-25	ヤンセンファーマシューティカエヌ．ベー．	鎮痛処置用プロキネチシン１受容体アンタゴニスト
JP6075621B2 (ja)	2010-08-10	2017-02-08	塩野義製薬株式会社	新規複素環誘導体およびそれらを含有する医薬組成物
EP2604595B1 (en)	2010-08-10	2016-03-16	Shionogi&Co., Ltd.	Triazine derivative and pharmaceutical compound that contains same and exhibits analgesic activity
TWI637949B (zh)	2013-06-14	2018-10-11	塩野義製藥股份有限公司	胺基三衍生物及含有其等之醫藥組合物
WO2015099107A1 (ja)	2013-12-26	2015-07-02	塩野義製薬株式会社	含窒素６員環誘導体およびそれらを含有する医薬組成物
BR112017022654A2 (pt)	2015-04-24	2018-07-10	Shionogi & Co., Ltd.	derivado heterocíclico de 6 membros e composição farmacêutica compreendendo o mesmo
JP7212930B2 (ja)	2016-04-06	2023-01-26	ザリージェンツオブザユニバーシティオブカリフォルニア	プロキネチシン２アゴニストおよびアンタゴニストを使用する概日および日周リズムの障害を処置するための組成物および方法
EP3527568A4 (en)	2016-10-17	2020-03-18	Shionogi & Co., Ltd	BICYCLIC NITROGEN HETEROCYCLIC DERIVATIVE AND PHARMACEUTICAL COMPOSITION COMPRISING SAME
WO2022138988A1 (ja) *	2021-04-14	2022-06-30	塩野義製薬株式会社	ウイルス増殖阻害作用を有するトリアジン誘導体およびそれらを含有する医薬組成物

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US7115560B2 (en)	2003-03-25	2006-10-03	The Regents Of The University Of California	Methods for modulating gastric secretion using prokineticin receptor antagonists
EP1866290B1 (en) *	2005-03-24	2013-05-01	Janssen Pharmaceutica N.V.	Prokineticin 1 receptor antagonists
WO2006102112A2 (en) *	2005-03-24	2006-09-28	Janssen Pharmaceutica N.V.	Prokineticin 1 receptor
EA200702062A1 (ru) *	2005-03-24	2008-02-28	Янссен Фармацевтика Н.В.	Пиримидиндионовые производные как антагонисты прокинетициновых рецепторов
WO2007067511A2 (en) *	2005-12-06	2007-06-14	Merck & Co., Inc.	Morpholine carboxamide prokineticin receptor antagonists
AR058407A1 (es) *	2005-12-29	2008-01-30	Janssen Pharmaceutica Nv	Antagonistas del receptor de proquineticina 2
CN101495464B (zh) *	2005-12-29	2014-03-05	詹森药业有限公司	激肽原1受体拮抗剂

2008
- 2008-10-23 CA CA2704185A patent/CA2704185C/en not_active Expired - Fee Related
- 2008-10-23 US US12/256,891 patent/US8324380B2/en active Active
- 2008-10-23 JP JP2010532152A patent/JP2011502154A/ja active Pending
- 2008-10-23 EP EP08844522A patent/EP2215067A1/en not_active Withdrawn
- 2008-10-23 WO PCT/US2008/080915 patent/WO2009058653A1/en not_active Ceased
- 2008-10-29 TW TW097141565A patent/TWI448456B/zh not_active IP Right Cessation
- 2008-10-30 AR ARP080104760A patent/AR069127A1/es not_active Application Discontinuation
- 2008-10-30 CL CL2008003266A patent/CL2008003266A1/es unknown
2012
- 2012-10-17 US US13/653,452 patent/US20140038968A1/en not_active Abandoned

Also Published As

Publication number	Publication date
CL2008003266A1 (es)	2009-10-16
EP2215067A1 (en)	2010-08-11
US20140038968A1 (en)	2014-02-06
US8324380B2 (en)	2012-12-04
WO2009058653A1 (en)	2009-05-07
TWI448456B (zh)	2014-08-11
AR069127A1 (es)	2009-12-30
JP2011502154A (ja)	2011-01-20
TW200934765A (en)	2009-08-16
CA2704185A1 (en)	2009-05-07
US20090163505A1 (en)	2009-06-25

Publication	Publication Date	Title
CA2704185C (en)	2016-02-16	Amino-heteroaryl-containing prokineticin 1 receptor antagonists
US8372973B2 (en)	2013-02-12	Prokineticin 1 receptor antagonists
US8362247B2 (en)	2013-01-29	Prokineticin 1 receptor antagonists
US20080287445A1 (en)	2008-11-20	Prokineticin 2 receptor antagonists
CA2602510A1 (en)	2006-10-05	Pyrimidindione derivatives as prokineticin 2 receptor antagonists
AU2006227394A1 (en)	2006-09-28	Prokineticin 1 receptor
HK1163688A (en)	2012-09-14	Prokineticin 1 receptor antagonists

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